Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

Apartments
Chalets
Cottages
Farmhouses
Homes
Barns
Boats
Bungalows
Cabins
Castles
Condos
Estates
Hotels
Lodges
Studios
Townhomes
Villas
Yachts

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Southold Vacation Rentals with Parking Included(85)

85 Results
Book it Now!
1 - 3 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
    (6)
    2 - 14 night minimum stay
    • 5 BR,
    • 4 BA,
    • Sleeps 10
      (10)
      2 night minimum stay
      • 4 BR,
      • 2 BA,
      • Sleeps 8
        (17)
        2 - 14 night minimum stay
        • 3 BR,
        • 1 BA,
        • Sleeps 6
          (9)
          2 - 3 night minimum stay
          • 3 BR,
          • 1 BA,
          • Sleeps 5
            2 - 7 night minimum stay
            • 3 BR,
            • 2 BA,
            • Sleeps 7
              (30)
              3 - 7 night minimum stay
              • 4 BR,
              • 2 BA,
              • Sleeps 10
                (3)
                2 night minimum stay
                • 2 BR,
                • 1 BA,
                • Sleeps 6
                  1 Review
                  3 - 7 night minimum stay
                  • 2 BR,
                  • 1 BA,
                  • Sleeps 5
                    $490 - $821
                    per night
                    Book it Now!
                    3 - 7 night minimum stay
                    • 4 BR,
                    • 3 BA,
                    • Sleeps 8
                      Book it Now!
                      • 3 BR,
                      • 3 BA,
                      • Sleeps 8
                        Book it Now!
                        3 - 5 night minimum stay
                        • 3 BR,
                        • 2 BA,
                        • Sleeps 6
                          (4)
                          3 - 7 night minimum stay
                          • 2 BR,
                          • 1 BA,
                          • Sleeps 4
                            (6)
                            7 night minimum stay
                            • 4 BR,
                            • 2 BA,
                            • Sleeps 8
                              (13)
                              2 night minimum stay
                              • 3 BR,
                              • 2 BA,
                              • Sleeps 6
                                (7)
                                2 night minimum stay
                                • 2 BR,
                                • 1 BA,
                                • Sleeps 4
                                  (9)
                                  • 3 BR,
                                  • 2 BA,
                                  • Sleeps 6
                                    1 Review
                                    Book it Now!
                                    2 night minimum stay
                                    • 3 BR,
                                    • 2 BA,
                                    • Sleeps 6
                                      Book it Now!
                                      5 - 7 night minimum stay
                                      • 3 BR,
                                      • 3 BA,
                                      • Sleeps 8
                                        1 Review
                                        Book it Now!
                                        2 - 3 night minimum stay
                                        • 2 BR,
                                        • 1 BA,
                                        • Sleeps 4
                                          (9)
                                          2 - 3 night minimum stay
                                          • 2 BR,
                                          • 1 BA,
                                          • 1 HF BA,
                                          • Sleeps 6
                                            (38)
                                            Book it Now!
                                            2 - 3 night minimum stay
                                            • 2 BR,
                                            • 1 BA,
                                            • Sleeps 4
                                              (3)
                                              Book it Now!
                                              7 - 14 night minimum stay
                                              • 4 BR,
                                              • 3 BA,
                                              • Sleeps 6
                                                2 Reviews
                                                $300 - $350
                                                per night
                                                Book it Now!
                                                3 night minimum stay
                                                • 3 BR,
                                                • 2 BA,
                                                • 1 HF BA,
                                                • Sleeps 8
                                                  5 - 7 night minimum stay
                                                  • 3 BR,
                                                  • 2 BA,
                                                  • 1 HF BA,
                                                  • Sleeps 8
                                                    (3)
                                                    2 - 5 night minimum stay
                                                    • 2 BR,
                                                    • 1 BA,
                                                    • Sleeps 6
                                                      (14)
                                                      2 - 7 night minimum stay
                                                      • 4 BR,
                                                      • 3 BA,
                                                      • Sleeps 13
                                                        (5)
                                                        2 night minimum stay
                                                        • 2 BR,
                                                        • 1 BA,
                                                        • Sleeps 4
                                                          (7)
                                                          2 night minimum stay
                                                          • 2 BR,
                                                          • 1 BA,
                                                          • Sleeps 4
                                                            (10)
                                                            2 - 7 night minimum stay
                                                            • 3 BR,
                                                            • 2 BA,
                                                            • Sleeps 6
                                                              (3)
                                                              Advertisement
                                                               

                                                              Recent Southold Reviews

                                                              Wonderful cottage - perfect location!

                                                              5 of 5
                                                              My husband and I enjoyed our week long stay at the cottage. Comfortable and cozy with easy access to wineries, restaurants and the beach! Added bonus of the hot tub and lake make it a perfect get away.
                                                              • Submitted: Sep 4, 2014
                                                              • Stayed: Jul 2014

                                                              Great house, great vacation

                                                              5 of 5
                                                              We couldn't have been happier with this house! The owner Freddie has made a lovely home that a vacationer feels welcome in and looks forward to coming to at the end of a beautiful beach day or a trip to the wineries. The kitchen is well equipped, the deck and grill are fantastic and Freddie's detailed welcome guide book is very helpful. Can't wait to stay here again!
                                                              • Submitted: Sep 1, 2014
                                                              • Stayed: Aug 2014

                                                              Lovely House

                                                              5 of 5
                                                              5 of us make friends stayed here and used it as a base for golf. Beautiful house and location and Chuck was extremely helpful and welcoming. We hope to go back.
                                                              • Submitted: Aug 21, 2014
                                                              • Stayed: Jul 2014